1. Field of the Invention
The invention relates to new chemical compounds which are of value as antibacterial agents. More particularly, it relates to novel bis esters of hydroxymethyl carbonate, HOCH.sub.2 OCOOCH.sub.2 OH, in which one hydroxy group is esterified with the carboxy group of penicillanic acid 1,1-dioxide and the other hydroxy group is esterified with the carboxy group of an alpha-aminopenicillin.
2. Description of the Prior Art
Penicillanic acid 1,1-dioxide (sulbactam) is known from U.S. Pat. No. 4,234,579 to be an effective beta-lactamase inhibitor and antibacterial agent.
In U.S. Pat. No. 4,244,951 and British Patent Application No. 2,044,255 bis esters of the formula: ##STR2## are disclosed in which sulbactam is coupled to known antibacterial penicillins via methanediol. In the above formula R.sub.1 represents certain acyl groups of known antibacterial penicillins e.g., 2-amino-2-phenylacetyl or 2-amino-2-(p-hydroxyphenyl)acetyl.
In copending application Ser. No. 300,421, filed Sept. 9, 1981 and assigned to the same assignee, compounds of formula (VII) are disclosed wherein R.sub.1 is: ##STR3## and R.sub.2 is certain alkyl or alkoxy groups.
In U.S. Pat. No. 3,928,595 antibacterial compounds are disclosed in which two penicillin or two cephalosporin molecules are bridged via a carbonate ester. These compounds are of the formula: ##STR4## where R.sub.4 is H, CH.sub.3 or C.sub.2 H.sub.5 and R.sub.3 is the residue of a penicillin or cephalosporin.
Ampicillin, 6-[D-(2-amino-2-phenylacetamido)]penicillanic acid is disclosed in U.S. Pat. No. 2,985,648. Amoxicillin, 6-[D-(2-amino-2-[p-hydroxyphenyl]acetamido)]penicillanic acid is known from U.S. Pat. No. 3,192,198 and U.S. Pat. No. Re. 28,744. p-acyl derivatives of amoxicillin are disclosed in U.S. Pat. No. 2,985,648, U.S. Pat. No. 3,520,876 and U.S. Pat. No. 4,053,360.